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AssigneeProduits Chimiques Ugine Kuhlmann
InventorsLouis Foulletier, Jean-Pierre Lalu
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The invention comprises perfluoroalkyl substituted amines of the formula ##STR1## wherein n is an integer from 1 to about 20, m is an integer between 2 or 4, R.sup.1 and R.sup.2 each is a hydrogen atom or a lower alkyl containing 1 to 3 carbon atoms and R.sup.3 and R.sup.4 each is a hydrogen atom, an alkyl containing 1 to 20 carbon atoms, an alkenyl containing 3 to 10 carbon atoms, a cycloparaffin radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 5 to 12 carbon atoms, and N or O ring substituted cycloalkenyl radical containing 5 to 12 carbon atoms, or an aryl, or R.sup.3 or R.sup.4 are joined in the form of an alkylene radical of the formula --(CHR).sub.p -- wherein p is an integer from 2 to 6 and R is a hydrogen atom or a lower alkyl containing 1 to 3 carbon atoms. These compounds are prepared by reacting at a temperature in the range between 0.degree. to 200.degree. C. perfluoroalkyl halides of the formula C.sub.n F.sub.2n+1 (CR.sup.1 R.sup.2).sub.m Y (II) wherein n, m, R.sup.1 and R.sup.2 each has the same meaning as defined hereinabove and Y is an iodine or a bromine atom with amines of the formula ##STR2## wherein R.sup.3 and R.sup.4 have the same meaning as previously stated. The invention also comprises perfluoroalkyl substituted amines of the formula ##STR3## and mixtures of products of formula IV with ##STR4## in which R.sup.1, R.sup.3 and R.sup.4 have the same meaning as designated above and where n is an integer from 4 to 20. The process for producing the products of formulas IV and V and mixtures thereof is the same as that used for the products of the compounds of formula I except that in the starting compounds of formula II at least one of the radicals R.sup.1 or R.sup.2 is hydrogen, m is equal to 2 and n is an integer between 4 and 20.
A perfluoroalkyl substituted amine of the formula ##STR30## wherein n is an integer from 1 to about 20, m is 2 or 4, R.sup.1 and R.sup.2 each is hydrogen or alkyl containing 1 to 3 carbon atoms and R.sup.3 is hydrogen and R.sup.4 is hydrogen or alkenyl containing 3 to 10 carbon atoms.
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
Of unsaturated carboxylic acid amides or imides: containing fluorine
General methods of organic chemistry: other general methods
And acyclic: with only one hydroxy group and one amino group bound to the carbon skeleton
The carbon skeleton being unsaturated: and acyclic
Term ended 22 Nov 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
I. Field of the Invention
This invention relates to mixtures of perfluoroaliphatic substituted amines and the method for preparing the same.
II. Description of the Prior Art
Further to illustrate this invention specific examples are described hereinbelow. The following examples, 1-9, also produce mixtures of saturated and unsaturated perfluoroaliphatic amines as reported in examples 20-30. However, the corresponding unsaturated amines were not separated or recovered therefrom and therefore the yields reported for the saturated perfluoroaliphatic amines are in fact the yields of the mixture. Examples 31-34 did not yield a mixture of amines.
A mixture of C.sub.6 F.sub.13 --C.sub.2 H.sub.4 I (47.4 grams, 0.1 mole) and n-butylamine (29.2 grams, 0.4 mole), dissolved in 100cm.sup.3 of amylalcohol, was heated with reflux and under continuous agitation at 113.degree. C. for 8 hours. This mixture was then distilled from which there were obtained three fractions and a semi-solid residue.
a. 41.degree. C/190 mm Hg. fraction: this fraction was washed with water, which yielded an aqueous phase at the top and a more dense organic phase. The organic phase, after drying over anhydrous sodium sulfate, weighed 6.5 grams; it was made up 98 percent of C.sub.6 F.sub.13 --CH.dbd.CH.sub.2.